


Making Money

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Anal Sex, Angst, Bad Parent John Winchester, Barebacking, Bondage, Bottom Dean, Butt Plugs, Cock Cages, Collared Dean, Dean Has Self-Worth Issues, Dean Winchester's First Time, Dean in Panties, Dehumanization, Dirty Talk, Fingering, First Time Bottoming, Gangbang, Gloryhole, Handcuffs, Humilation, Hurt Dean, Leashes, Loss of Virginity, M/M, Morally Bankrupt John Winchester, Multi, Name Calling, Objectification, Orgasm Denial, Prostitute Dean, Prostitution, Public Humiliation, Public Nudity, Restraints, Rough Sex, Semi-Public Sex, Size Difference, Size Kink, Sounding, Teen Dean, Training, Unsafe Sex, noncon
Language: English
Status: Completed
Published: 2017-06-04
Updated: 2017-06-04
Packaged: 2018-11-09 01:12:02
Rating: Not Rated
Warnings: Underage
Chapters: 1
Words: 4,709
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11093790
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: John had found a fast way to make money and it took barely any effort on his part once he'd set everything up. He knew, deep down, that it was wrong to exploit Dean in such a way but they needed ways to make money to survive on if he was to find the demon who killed Mary.





	Making Money

**Author's Note:**

> READ THE TAGS BEFORE CONTINUING!
> 
> Written for multiple prompts.
> 
> Eight of you requested underage bottom Dean in a gloryhole. Four of you specifically wanted John putting him in there to make money. Most of you had various kinks you wanted included and all of you wanted noncon. Since the varying requests all had several different requests in common I combined all of the prompts into one and I managed to get every single kink requested in this.

“Why is Sam staying with Bobby?” Dean asked as the Impala finally pulled into a parking spot. He could see a bright red sign, for a bar, and men lingering around the door. His Dad turned the Impala off, reached into the backseat and pulled a bag into the front. “Dad?”

“We’re going to start a different kind of training, Dean.” The sound of John digging into a bag drew Dean’s attention from the men outside of the bar and their new surroundings. “Come on, out of the car.”

Dean was quick to comply. He climbed out, shut the door and waited as his Dad walked around the car to open the backseat. The bag rested on the top of the car as his Dad eyed him. “What kind of training?”

“You need to start helping me make money. We have to afford food, clothing, gas and places to stay, Dean. That isn’t getting into the cost for two educations.” Hands went to his pants and Dean froze, confused and unsure, as his Dad started to yank his pants down exposing him to the cool night air.

“Dad!” he started to stumble back, embarrassed and confused, but a stern look from his Dad stopped him. “Why ar—”

“I thought I had raised a more grateful son.” The look of disapproval had shame curling inside of him and Dean looked down, cheeks flushed and hands hovering in front of his exposed front.

“What do I need to do?”

“That’s a good boy.” Now the tone was full of approval and Dean mentally preened at it. He _was_ good. He could be good. His Dad would never steer him wrong and this wasn’t any different. Whatever he said needed to be done Dean would do. “Open your mouth,” Dean slowly opened his mouth only to have a red ball pushed in. It filled his mouth and stretched his jaw. His Dad secured it in place in seconds. “Now bend over the seat. I have to prepare you before we go in.”

Dean’s heart was pounding in his chest as he turned, laid over the seat and pressed his face against it as he struggled to control his increasingly fast breathing. The large ball in his mouth was causing his jaw to ache and he wanted it out.

A wet finger rubbed against his hole and Dean jolted, shocked, as it rubbed and then started to push inside. _It burned_. He squirmed, clenching and whining, as a heavy hand landed on the small of his back and kept him in place.

“You’re going to need to be thoroughly prepared before we go inside. It’ll make your training far easier and you don’t want any damage down there.”

He didn’t have any idea what this had to do with training but Dean could be good. That didn’t stop the whimpering and muffled cries that escaped him as his Dad worked one finger in, curling it and pumping, until he could push a second in.

Dean’s muffled sounds of pain filled the Impala as his Dad held him in place, adding fingers and lube, until a sound of satisfaction escaped. “That should be good enough. Now for the final touches. A thick plug should keep you ready.”

Something wet, hard and round pushed against his aching hole as his Dad worked it inside. It pushed deep and settled inside of his ass, the end catching on his rim as he clenched and whined.

Strong hands hauled him up and turned him around. “You don’t need that.” His shirts were pulled off, tossed into the Impala, before his Dad dug around in a bag. “We’ll get more money if you look the part.”

Dean stopped himself from flinching when his Dad picked up his small cock but he couldn’t stop the flinch when his Dad started trying to work something inside. “ _Dad_!” his protest was muffled by the gag but Dean was trying to get his Dad’s attention. He swayed back, pushing against the side of the car, as his Dad kept a firm hold.

“You need to relax and stay still, Dean, or this will hurt.”

He mumbled into the gag _It already hurts_ and it must have been clear enough that his Dad understood him.

“That’s because you’re not obeying me.”

He bit his lip, closed his eyes and waited. Dean could feel whatever it was working into his cock and then cool metal was settled around his cock. It ached. His Dad’s hands next went to his balls, gripping them and Dean didn’t protest as a metal band was secured around them.

Dean reached down, touched it and hated how it looked. He tried asking what it was and was thankful when his intent was understood once again.

“That is a cockcage with a sound. Men like the look of it.” That was the only explanation. “They like when young, pretty boys are locked up and gagged while they’re used.”

That didn’t seem to have anything to do with training. He’d been taught to shoot, fight and the various symbols needed for hunting. This had nothing to do with that but his mind refused to understand what was happening. His Dad couldn’t possibly lead him wrong.

“Step.” Dean blindly stepped and stepped again when directed. He could feel soft material moving up his legs until it covered his ass. His Dad had put light pink translucent panties on him.

Humiliation filled him and Dean’s cheeks flushed with shame. He looked away as his Dad hummed in satisfaction and reached into the bag once more. A matching pink collar, something that looked like it belonged on a female dog, was wrapped around his neck and then a set of handcuffs with a chain attached bound his wrists in front of him.

“There we go. Now you’re ready.”

A tug on the chain had Dean reluctantly following behind his Dad, wishing he could cover up or better yet climb back into the Impala. As they approached the entrance several of the men outside stared at him, leering, while Dean ducked his head and twisted his hands where they were cuffed. He stumbled over the threshold when his Dad tugged on the chain after he’d paused, staring at a bar full of men only. All eyes seemed to be on him as his Dad lead him through the room, hands brushing against his bare skin and several over his ass.

His Dad walked up to the bar, still leading him by his cuffs, to address a large man behind the bar who made Dean think of a biker. “I was told four hours for four hundred.” Dean shifted closer to his Dad, feeling hands trailing along his body and noticing quite a bit of attention turned towards him.

The large man leaned over the bar, eyes roving over him, as a smile pulled at his rough face. “I knew you were bringing in a young, fresh one to have him trained but I didn’t know your whore was so… _pretty_. You offer _him_ back in the gloryhole we discussed until closing and I’ll give you a thousand. The spike in business will be more than worth it.”

Dean’s ass clenched down on the plug inside of him and his face heated as he caught several comments about his appearance. He didn’t hear them talking until his Dad tugged him, “Dean, stand still.” A camera flashed once his Dad had moved him several feet away. Then he found himself turned and bent over. Another flash. Humiliation choked him and his face heated at the position.

“That’s good. I’ll get that up on the site immediately. Letting the customers know what the whore on offer looks like helps increase business in the back. After I get him set up I’ll give you the password so you can access the page and approve the post.”

He stood once his Dad gave the order and quickly moved closer, trying to conceal his body, as the man behind the bar walked around. His Dad handed over the chain to the man, accepted a roll of cash and sat on a bar stool.

“I expect you to follow his instructions to the letter. Be good, remember what you learn tonight and we’ll come back tomorrow. The Impala needs some repairs and your help is important in paying for them. You’ll get used to earning money after a few days of solid training and hands-on experience. This is the best way for you to earn your keep and help out. You were not given looks like that for nothing.” A tremor ran through Dean’s body when the stranger tugged on the chain and started leading him through the bar.

“Look at that pretty boy.”

“I’m looking forward to taking a turn in that pert little ass.”

“I knew tonight was going to be good. Such a pretty little thing.”

“The whores they usually have don’t look near that tempting. Can't wait to ruin 'im.”

They went through a doorway, down a hallway and into a room. Dean could hear moaning, the sounds of skin smacking and even more filthy words. “We have two special stalls for fuckable little things like you that men are willing to pay to use.” The man’s voice was rough and those eyes moved over his body. Dean squirmed under the stare. “Tomorrow I’ll move the bench to the double ended stall for paying customers so you can learn to kill that gag reflex of yours. A useless thing for a whore. Your pimp said tonight is just training your ass and getting you used to taking dick like a pro.”

Dread filled Dean as he tugged on the chain, wanting to run back into the bar and out the door but the man kept pulling him along. He found himself in a small stall, a bench with straps set up against a wall with a hole.

Large hands hauled him up easily, laid him down on the bench so his ass was pressed right up against the hole and as Dean froze, heart pounding and a rushing sound in his ears, the man secured a strap around his middle. It tightened, keeping him in place and then his legs were both being secured down with two more straps. Dean snapped out of it and started to jerk, flight instincts screaming that he move, as his wrist was freed from the handcuffs.

But a hand was quick to curl around his wrist, dragged his arm down and secured his right arm down and then his left. Dean jerked at the restraints, muffled protests filling the stall, as the man frowned.

“Fuck. Forgot to remove those.” He stepped out of the stall, disappeared and Dean was left alone in a stall in a large room echoing with moans and grunts. Dean tugged and writhed, trying to get off the bench, until the door was opening and the man returned with a pair of scissors. “Don’t move. You don’t want to be cut.”

_Snip_

_Snip_

The lace panties were in shreds and ended up discarded. Dean protested. He didn’t _care_ about being good. He wanted out, he wanted back in the car and he wanted to be back at Bobby’s with Sam. His Dad would understand that he was terrified. He wasn't ready for something like this.

“By the time you’re let out of here that hole of yours is going to be well trained and used to taking all kinds of dick.” There was a rougher tone to the man’s voice as a hand ran up the length of his body and down to the swell of his ass. “Need to remove that plug, add some lube but I’ll let them know this stall is available for use.”

The door shut, locked and Dean was left in a low-lighted stall, completely strapped down and naked with his heart trying to pound right out of his chest.

He felt a tug on his hole and the round end of the plug edged out, popped free and cold, wet fingers slipped into his ass. Dean tensed, yanking on his restraints and tightening down, while the fingers pumped into him and finally, mercifully disappeared before something pressed up against his ass again. Cold wetness seemed to flood his ass and Dean jerked again, whimpering and clenching, before the object was removed and a hum of satisfaction barely reached him over the other noises in the room.

Dean’s breathing was ragged, his cheeks flushed and his body was thrumming with tension. He could still hear moans and grunts, curses and banging, as he laid there and waited.

This wasn’t training. This wasn’t any kind of training. This was some kind of punishment because his Dad was angry at him for messing up the last hunt. Dean _knew_ that was what this was and if his Dad would just let him apologize, just let him explain, they could go back to Bobby’s without needing to do whatever this was.

There was a swiping kind of sound, a beep and then the sound of a door banging open, “I hoped I’d get the first go at _your_ ass, little whore. Look how sloppy and wet they have you. You're going to feel _so fucking good_ wrapped around my dick.” Dean squirmed when fingers rubbed around his rim, dipped inside and then something blunt, round and large pushed against him. “Saw you walking through the bar and knew I’d pay whatever fee they were charging to use you.”

The blunt thing started sinking in, burning and aching violently, as he tensed and tried to move away. _Stop! Please stop stop stop it hurts!_ He tried protesting but the gag kept his mouth full and the only sounds that escaped were muffled, pained moans. Tears burned the backs of his eyes.

“Fuckin’ tight and so fuckin' wet. Usually we don’t get such a treat in here but I’m not going to question my luck.” Dean realized belatedly, the words coming back to him, that the man was pushing his _cock_ into his ass and Dean wanted it out. “Completely worth the fee.”

He wanted it out _now_. This wasn't right. This was _wrong wrong wrong._

“First fuck is _always_ the best in a tight hole like yours. You’ll be ruined after enough dicks get in you even if I like them sloppy.”

The man on the other side bottomed out inside of him with a groan as Dean whined and panted into his gag, body tense and mind screaming in protest at the pain of having the man's cock buried completely inside of his aching ass. Slowly the man drew back, inch by inch disappearing and then he slammed deep again.

Dean grunted into his gag at the force behind the thrust, body writhing on the bench, as the man started to pound into his aching ass. His cheeks heated, tears burned his eyes but the man didn’t stop. Instead the sound of pleased moans and grunts sounded from behind the wall. “Nothin’ like breakin’ in a whore.” The thick, long cock ruthlessly pumped in and out of his ass as Dean laid there strapped down in his stall. “Your pimp is lucky to have found such a sweet little thing like you to sell. Good to start trainin' them when they're young, soft and malleable.”

He had never been sorrier to screw up a hunt.

This was the worst punishment his Dad had ever given him for making a mistake and Dean wanted to beg him to make it stop. He wanted to tell his Dad he’d do anything, _anything_ to make it up if he could leave. He’d even bend over the bed and quietly take a beating with his Dad’s belt if it meant _this_ stopped.

“Like a vice.” The man’s voice was rough, “Wish I could see that delectable little body while I’m fuckin' your sweet hole. Guess I’ll have to hope to find you when you’re turnin' tricks on the street.”

The pace became faster, rougher, as the man continued to thrust into him and Dean whined into his gag. His wrists hurt from where he yanked on his restraints and his ass burned from the painful stretch of being filled.

Then the man slammed deep, a loud and filthy groan escaping, before the cock inside of him pulled out and Dean’s ass clenched down on reflex. It hurt, his hole gaping and leaking come, as he lay there panting and whimpering in pain.

Dean turned to stare at the door to the stall he was tied down in, waiting for the man from the bar or his Dad, but neither opened the door and instead the door to behind him banged open again after a beep.

Another cock pushed in and the pain started up once more.

The sound of a swipe and beep was the only warning Dean received as man after man after man filled the other stall, each of them pushing into his increasingly sloppy and painful hole, while Dean fought against his restraints until he was exhausted and could only lie there, whimpering and whining, as he was fucked without an ounce of energy left to resist. His jaw ached from the ball filling his mouth, his wrists were rubbed raw, his middle where the strap held him in place stung and his hole throbbed. Silent tears spilled from his eyes, running down his cheeks and dripping onto the padded bench. This was a nightmare. A horrible, painful nightmare and no one could hear his muffled sobs over the sounds of pleasure and fucking filling the room.

It was hours of humiliation, pain and the sensation of men pushing into him, thrusting and eventually emptying their release into his hole that felt as though it had been fucked raw.

Dean’s cheek rested against the padding, body limp, as each hard thrust into his ass forced a grunt and a whine out of him. He tried moving his hips, to get the painful pressure off of his cock but he couldn’t move much and was forced to stay in the same position.

“Gotta love a sloppy little whore.” The man on the other side’s voice was rough with a satisfied tone as he pumped his cock in and out of Dean, banging against the wall, and groaning as he took pleasure. “I always like ‘em when they’re fucked open and used.”

Six more thrusts, a loud and low groan, and the cock lodged in his ass disappeared. Come lazily leaked out of his gaping hole and Dean rested on the bench, knowing it wouldn’t be long, until he heard the swipe, beep and the door banging open.

It was only minutes before another man was thrusting away inside of him. Soft, choked whimpers and whines escaped him as his tired body took another round of rough fucking.

He wasn’t sure how long he stayed in the stall, tied down and used, until the other sounds of pleasure filling the room faded and the door to the stall he was in unlocked, opened and the large man from before came in. Dean had lost track of how many men had pushed inside of him at twenty five and that was hours ago.

“I knew giving your pimp a thousand would earn me even more. I made a killing tonight charging for you on top of the added sales from the bar. Don’t think I’ve ever let a pimp use the gloryhole for a whore that brought in so much business. You wouldn't believe how many men have come in that tight ass of yours tonight. I didn't think the site could possibly bring so many in on your first night but you are a very popular little whore it seems.”

The straps on his legs were undone first, then his right wrist which was immediately cuffed and his left received the same treatment. A few seconds later the one around his middle was gone and Dean was scooted up, the plug from before pushed into his ruined hole and large hands hauled him up.

Dean swayed, pitched forward and found himself caught in the man’s arms as his legs failed to support him. “Woah there.” A chuckle escaped the man, “Looks like all those men fucked that little hole of yours good.” Dean had to stumble along after the man, yanking on the chain and pulling him out of the large room.

Each step sent bolts of pain racing up his back and his ass painfully reminded him exactly how he’d spent hours and hours. A glance at the clock revealed it was past three. Dean’s eyes were drooping, his mind and body exhausted, as he was lead back into the bar.

It was empty.

“Your pimp said I’d get one fuck after and then to let him know you’re done for the night.” Dean tried to protest, hands weakly pushing at the man but it didn’t matter. He was bent over a bar stool, chain wrapped around it and ass offered up. “There we go. Now be a good whore and let me collect my fee.”

The plug popped free causing Dean to jerk, whining at the feeling of it spreading his hole open on its exit. Come started to leak back out until the man stepped forward and guided his hard cock inside.

Dean clenched his eyes shut, fingers curling and gut churning, as a loud, filthy groan of bliss followed when the man started sinking in until warm balls pressed up against Dean’s wet ass.

“Fuck.” The word was hissed, “I can see why there were repeats going back there. Such a fuckable ass and they didn’t even get to see you like _this_ when they were using you. Over eight hours of use and you still feel amazing. You can't get that kind of use for a whore on a street corner like you can renting a stall in a gloryhole.”

Fingers dug into his hips as the man moved back and then slammed forward with a hard, vicious snap. Dean jolted on the bar stool, body swaying, as the first few thrusts were almost lazy. Then the man from the bar was viciously, roughly pounding into him and moaning loudly with each fuck forward.

“Fuck. Fuck you feel so good.” the words were full of arousal, “I can see why your pimp wanted you more experienced before putting you to work collecting johns.” Balls slapped wetly against his ass while the man’s cock swiftly fucked into him. “You want a whore like you with some experience. Can’t waste a whore with such potential. Start ‘em early, train them hard and you’ll make more money. He'd be better off only putting you on a corner to work some nights and renting a gloryhole the rest of the week. More money that way.”

Tears ran down his cheeks as Dean silently cried, pain still filling him but his exhausted body wasn’t letting him do anything else than lie there taking it. It’s what he’d had to do all night.

The last one seemed to take forever, the man using him dragging it out, until finally, mercifully, the man slammed deep with a loud grunt. His hips jerked forward a few times, curses escaping, before the softening cock pulled out. Dean’s plug was pushed back in and the man left him there.

“Yeah. Your whore is done for the night. You can come collect him.”

Dean didn’t bother to move. He laid there and waited until the sound of the door had him glancing over to see his Dad coming over. “Did he follow your instructions?”

“Yeah. The little whore earned his money tonight. I’ll have everything ready in the double ended stall for,” he chuckled at the clock, “tonight. Do you have a ring gag?”

“Of course. I’ll have him ready to work. Same time?”

“I’ll advertise him all day. Bring him in early, about four, and I’ll have a line waiting for him. He'll be in full use for eleven hours if you're interested in getting more out of him.”

“If he comes in that early and stays till closing a thousand isn’t going to cut it especially with them getting to fuck at both ends.” Dean listened to his Dad haggling over a price. He closed his eyes and held back a sob.

The man hummed lowly, “I’ll have a number for you when you bring him in that I know will work for both of us.”

“Alright. I really like this set up and would hate to have to take him elsewhere.”

“Understandable. You want the money he’s worth.” The man shifted some papers, “You’ve got yourself a very fine whore right there. It’s good to start them younger, get them used to taking dick and being good at servicing men if you want to make a decent amount. That one…he’s got the looks, mouth and ass to make you a lot of money for _years_. Anytime you want to install him here for the night to make a flat fee I’d be more than happy to pay you. Once that picture was up for the gloryhole offerings my business increased significantly. There was barely a minute between men finishing and a new one taking a turn at using him.”

Dean didn’t look at his Dad but he hated the way they were talking about him. Like he was an object instead of a person. “Thanks. I was a bit worried about him but I think a few more nights in a gloryhole will get him used to earning money on the end of a dick.”

His Dad’s footsteps came closer after a few more minutes of talking, the chain was unwrapped and Dean was guided off the bar stool. He stumbled, whining into the gag, as his Dad led him out of the bar and across the parking lot to the waiting Impala.

He said nothing when a blanket was wrapped around him and he was laid out in the backseat. A soft sound of protest escaped when his abused ass pushed against the seat. “You did good tonight, Dean. You earned a good living working hard and using that body you were blessed with.” Dean could hear the praise in his Dad’s voice and hated how it made him feel warm, _loved_ , even when every single inch of him hurt horribly and he felt sick to his stomach. “You’ll get used to whoring. This is the fastest way to earn money so we can find that monster who killed your Mom and make sure Sammy is taken care of. It’s luck you’re so pretty. Men will pay all kinds of money for someone who looks like you. Whoring is the very best option for you and you'll be good at it. With enough training and use you might even come to love whoring.”

Dean closed his eyes and hated himself. If he wasn’t _pretty_ this would have never happened. He would be able to help his Dad earn money some other way. If he wasn't pretty he wouldn’t be coming back here, again and again, for the same kind of humiliating torture to earn money.

“You’ll get used to it. Soon enough you’ll be working a corner when you get a chance, pulling in all kinds of money and everything will work out. You’re learning skills, how to pleasure a man, that’ll help you make enough money over the years to help your family. Don't worry. I spoke to that bar owner and he gave me a huge list of other gloryholes across the country who provide the same service where a whore can earn their money in the back. You won't have to work a street corner every night. Most nights I'll take you to one of those gloryholes, you'll spend the night whoring in the backroom and you won't have to worry about spending time outside on a corner waiting for clients.”

If his Dad said anything else Dean didn’t hear it. The sound of the engine and the movement of the car dragged him into sleep quickly.

**Author's Note:**

> I didn't realize that gloryhole fics were so popular or that John prostituting Dean to fund his quest for revenge was widely sought. There were quite a few varying ages in the requests so I wrote Dean's age so it would be ambiguous and readers could choose whatever age they imagined. Not sure what age anyone is imagining but I hope it covered all the requesters' requirements.
> 
> I hope this fic met all of the prompters' requests and that you enjoyed my attempt to meet every kink/trope/etc in this. I actually made a check list to make sure I got every thing in this.


End file.
